Kyushu University [Hiroyuki Morimoto (Lecturer) Faculty of Pharmaceutical Sciences, Department of Chemo-Pharmaceutical Sciences]

Development of Novel, Environmentally-Benign Catalytic Reactions
keyword : Synthetic Organic Chemistry, Catalysis, Enantioselective Synthesis
2010.07～2015.06.

Academic Activities

Books

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1.	大嶋孝志, 森本浩之, 森崎一宏, Catalytic Asymmetric 1,2-Alkynylation, Elsevier, 10.1016/B978-0-12-409547-2.11504-5, Reference Module in Chemistry, Molecular Sciences and Chemical Engineering, 2015., 2015.02, [URL].

Reports

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1.	森崎　一宏, 森本浩之, 大嶋孝志, 真島　和志, Direct Enantioselective Alkynylation of α-Ketoesters and α-Ketiminoesters Catalyzed by [Bis(oxazoline)phenyl]rhodium(III) Complexes, Heterocycles, 2017.01.

Papers

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1.	Tetsuya Kadota, Masanao Sawa, Yuta Kondo, Hiroyuki Morimoto, Takashi Ohshima, Catalytic Enantioselective Strecker Reaction of Isatin-Derived N-Unsubstituted Ketimines, Organic Letters, 10.1021/acs.orglett.1c01194, 2021.06, A catalytic enantioselective Strecker reaction of isatin-derived N-unsubstituted ketimines directly afforded the N-unprotected α-aminonitriles with a tetrasubstituted carbon stereocenter in up to 99% ee without requiring protection/deprotection steps. One-pot Strecker reactions from the parent carbonyl compounds were also realized with comparable yields and enantioselectivities. Direct transformations of the N-unprotected α-aminonitrile products streamlined the synthesis of unnatural amino acid derivatives and achieved the shortest one-pot stereoselective routes to a biologically active compound reported to date..
2.	Morisaki, Kazuhiro; Morimoto, Hiroyuki; Ohshima, Takashi, Recent Progress on Catalytic Addition Reactions to N-Unsubstituted Imines, ACS CATALYSIS, 10.1021/acscatal.0c01212, 10, 12, 6924-6951, 2020.06, Catalytic addition reactions to N-unsubstituted (N-unprotected) imines can provide a more straightforward synthesis of amines. This direct process eliminates the unnecessary protecting-group manipulations that are required with N-substituted (N-protected) imines and can contribute to the development of green chemistry. Although their use has been limited due to difficulties associated with the nature of N-unsubstituted imines, recently developed catalytic methods enable the use of N-unsubstituted imines as electrophiles in various catalytic addition reactions. To facilitate an understanding of the state of the art development of synthetic methodologies, herein we review recent progress on catalytic addition reactions to N-unsubstituted imines. We begin with an overview of the chemistry of N-unsubstituted imines, followed by a summary of recent progress categorized according to the reaction type. We hope this review will help to stimulate further development of greener syntheses of nitrogen-containing compounds..
3.	Yuta Kondo, Tetsuya Kadota, Yoshinobu Hirazawa, Kazuhiro Morisaki, Hiroyuki Morimoto, Takashi Ohshima, Scandium(III) Triflate Catalyzed Direct Synthesis of N-Unprotected Ketimines, Organic Letters, 10.1021/acs.orglett.9b04038, 22, 1, 120-125, 2020.01, N-Unprotected ketimines are useful substrates and intermediates for synthesizing valuable nitrogen-containing compounds, but their potential applicability is limited by the available synthetic methods. To address this issue, we report a scandium(III) triflate catalyzed direct synthesis of N-unprotected ketimines. Using commercially available reagents and Lewis acid catalysts, ketones were directly transformed into the corresponding N-unprotected ketimines in high yields with broad functional group tolerance, even in multigram scales. The reactions were readily applicable for one-pot synthesis of important compounds such as a glycine Schiff base without isolation of N-unprotected ketimine intermediates. Preliminary mechanistic studies to clarify the reaction mechanism are also described..
4.	Masanao Sawa, Shotaro Miyazaki, Ryohei Yonesaki, Hiroyuki Morimoto, Takashi Ohshima, Catalytic Enantioselective Decarboxylative Mannich-Type Reaction of N-Unprotected Isatin-Derived Ketimines, Organic Letters, 10.1021/acs.orglett.8b02306, 20, 17, 5393-5397, 2018.09, The first catalytic enantioselective decarboxylative Mannich-type reaction of N-unprotected ketimines is reported, directly providing N-unprotected 3-tetrasubstituted 3-aminooxindoles in high yield and ee without protection/deprotection steps. The utility of this reaction is demonstrated in the short step synthesis of (+)-AG-041R..
5.	Toru Deguchi, Hai Long Xin, Hiroyuki Morimoto, Takashi Ohshima, Direct Catalytic Alcoholysis of Unactivated 8-Aminoquinoline Amides, ACS Catalysis, 10.1021/acscatal.7b00442, 7, 5, 3157-3161, 2017.05, Direct catalytic alcoholysis of unactivated amides is one of the most difficult challenges in organic chemistry, and an applicable method for cleaving amides used as directing groups in regioselective functionalization reactions has not been reported. Herein, we report direct catalytic alcoholysis of 8-aminoquinoline amides, which are highly effective directing groups in regioselective functionalization reactions. The reactions proceeded with a simple combination of substrates, air-stable catalysts, and alcohols, affording the corresponding esters in good yields with broad functional group tolerance. Highly chemoselective cleavage of the 8-aminoquinoline amides in the presence of related carbonyl functionalities and preliminary mechanistic studies are also described..

Presentations

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1.	◯ Hai-Long Xin, Toru Deguchi, Hiroyuki Morimoto, Takashi Ohshima, Direct Catalytic Alcoholysis of Unactivated 8 Aminoquinoline Amides, 日本化学会第98春季年会, 2018.03.
2.	◯Amrita Das, Kenji Watanabe, Hiroyuki Morimoto, and Takashi Ohshima, Boronic Acid-Accelerated Multicomponent Reactions for the Synthesis of α-Substituted Indole-3-acetic Acids, 第64回有機金属化学討論会, 2017.09.
3.	◯Megumi Noshita, Yuhei Shimizu, Hiroyuki Morimoto, Takashi Ohshima, Hydrazine and Diethylenetriamine Mediated Direct Cleavage of Unactivated Amides, Carbamates, and Ureas, 254th American Chemical Society National Meeting & Exposition, 2017.08.
4.	Hiroyuki Morimoto, Kazuhiro Morisaki, Masanao Sawa, Ryohei Yonesaki, Yuta Kondo, Kazushi Mashima, Takashi Ohshima, Construction of Tetrasubstituted Carbon Stereocenters via Direct Catalytic Nucleophilic Addition to Ketimines, 日本化学会第97春季年会, 2017.03.
5.	Hiroyuki Morimoto, Yuhei Shimizu, Megumi Noshita, Takashi Ohshima, Direct Cleavage of Unactivated Amides Under Mild Conditions, The 10th International Symposium on Integrated Synthesis (ISONIS-10), 2016.11.
6.	Kazuhiro Morisaki, Hiroyuki Morimoto, Takashi Ohshima, Zn-Catalyzed Direct Alkynylation of N-Unprotected Trifluoromethyl Ketimines, The 6th Junior International Conference on Cutting-edge Organic Chemistry in Asia (6th Junior ICCEOCA), 2016.10.
7.	Kazuhiro Morisaki, Hiroyuki Morimoto, Takashi Ohshima, Development and mechanistic studies of Rh-catalyzed direct enantioselective alkynylation of α-ketiminoesters, 252nd American Chemical Society National Meeting & Exposition, 2016.08.
8.	Masanao Sawa, Kazuhiro Morisaki, Ryohei Yonesaki, Hiroyuki Morimoto, Kazushi Mashima, Takashi Ohshima, Direct Catalytic Asymmetric Alkynylation of Ketimines, Molecular Chirality Asia 2016, 2016.04.
9.	Takashi Ohshima, Kazuhiro Morisaki, Masanao Sawa, Ryohei Yonesaki, Hiroyuki Morimoto, Rhodium-Catalyzed Direct Enantioselective Alkynylation of Ketimines: Mechanistic Studies and Expansion of Substrate Generality, The 2015 International Chemical Congress of Pacific Basin Societies (Pacifichem), 2015.12.
10.	Yuhei Shimizu, Megumi Noshita, Yuri Mukai, Hiroyuki Morimoto, Takashi Ohshima, Cleavage of Unactivated Amide Bonds by Ammonium Salt-Accelerated Hydrazinolysis, The 2015 International Chemical Congress of Pacific Basin Societies (Pacifichem), 2015.12.
11.	Kazuhiro Morisaki, Masanao Sawa, Ryohei Yonesaki, Jun-ya Nomaguchi, Yosuke Takeuchi, Hiroyuki Morimoto, Kazushi Mashima, Takashi Ohshima, Direct Catalytic Enantioselective Alkynylation of Ketimines, The 5th Junior International Conference on Cutting-edge Organic Chemistry in Asia (5th Junior ICCEOCA), 2015.11.
12.	Masanao Sawa, Kazuhiro Morisaki, Ryohei Yonesaki, Hiroyuki Morimoto, Kazushi Mashima, Takashi Ohshima, Direct Catalytic Asymmetric Alkynylation of Ketimines, 7th International Conference on Green and Sustainable Chemistry - 4th JACI-GSC Symposium, 2015.07.
13.	Takashi Ohshima, Kazuhiro Morisaki, Masanao Sawa, Rhohei Yonesaki, Hiroyuki Morimoto, Rhodium-Catalyzed Direct Enantioselective Alkynylation of Ketimines: Mechanistic Studies and Expansion of Substrate Generality, The 7th Spanish-Portuguese- Japanese Organic Chemistry Symposium (7th SPJ-OCS), 2015.06.
14.	Kazuhiro Morisaki, Masanao Sawa, Jun-ya Nomaguchi, Hiroyuki Morimoto, Yosuke Takeuchi, Kazushi Mashima, Takashi Ohshima, Rh-Catalyzed Direct Enantioselective Alkynylation of Ketimines, 第5回大津会議, 2014.10.
15.	Ming Zhang, Kenji Watanabe, Masafumi Tsukamoto, Ryozo Shibuya, Hiroyuki Morimoto, Takashi Ohshima, Pt-Catalyzed Allylic Aminations: Application to a Short and Practical Total Synthesis of (-)-α-Kainic Acid, XXXVI International Conference on Organometallic Chemistry (ICOMC2014), 2014.07.
16.	Kazuhiro Morisaki, Masanao Sawa, Jun-ya Nomaguchi, Hiroyuki Morimoto, Yosuke Takeuchi, Kazushi Mashima, Takashi Ohshima, Rh(III)/Phebox-Catalyzed Direct Enantioselective Alkynylation of α-Ketiminoesters, XXXVI International Conference on Organometallic Chemistry (ICOMC2014), 2014.07.
17.	Ming Zhang, Kenji Watanabe, Masafumi Tsukamoto, Ryozo Shibuya, Hiroyuki Morimoto, Takashi Ohshima, Short-Step Synthesis of (－)-α-Kainic Acid via　Pt-catalyzed Allylic Aminations, The Eighth International Symposium on Integrated Synthesis　(ISIS-8), 2013.11.
18.	Takashi Ohshima, Kazuhiro Morisaki, Masanao Sawa, Jun-ya Nomaguchi, Hiroyuki Morimoto, Yosuke Takeuchi, Kazushi Mashima, Rh-Catalyzed Direct Enantioselective Alkylation of α-Ketoiminoesters, 17th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS17), 2013.07.
19.	Takashi Ohshima, Kazuhiro Morisaki, Masanao Sawa, Jun-ya Nomaguchi, Hiroyuki Morimoto, Yosuke Takeuchi, Kazushi Mashima, Rh-Catalysed Direct Enantioselective Alkynylation of α-Ketiminoesters, Thieme Nagoya Symposium, 2013.05.
20.	Kazuhiro Morisaki, Masanao Sawa, Jun-ya Nomaguchi, Hiroyuki Morimoto, Yosuke Takeuchi, Kazushi Mashima, Takashi Ohshima, Rh-Catalysed Direct Enantioselective Alkynylation of α-Ketiminoesters, Twenty-third French-Japanese Symposium on Medicinal and Fine Chemistry (FJS-2013), 2013.05.
21.	Hiroyuki Morimoto, Risa Fujiwara, Yuhei Shimizu, Kazuhiro Morisaki, Takashi Ohshima, Lanthanum Triflate-Catalyzed Direct Amidation of Esters with Amines, Twenty-third French-Japanese Symposium on Medicinal and Fine Chemistry (FJS-2013), 2013.05.
22.	Takashi Ohshima, Yuhei Shimizu, Hiroyuki Morimoto, Ming Zhang, Deacylation of Unactivated Amides to Amines Using Ammonium Salt-Accelerated Transamidation, The 7th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-7)/The 3rd New Phase International Conference on Cutting-Edge Organic Chemistry in Asia (NICCEOCA-3), 2012.12.

Membership in Academic Society

The Pharmaceutical Society of Japan
The Chemical Society of Japan
The Society of Synthetic Organic Chemistry, Japan
American Chemical Society

Awards

Development of Direct Catalytic Asymmetric Mannich-type Reactions Using Trichloromethyl Ketones as an Ester Equivalent Donor

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